


What are friends for?

by zation



Series: SPN Kink Bingo 2018 [5]
Category: Supernatural
Genre: Alternate Universe - Modern Setting, Anal Fingering, Anal Sex, Bottom Dean, Cas is almost too good of a friend, Embarrassed Dean Winchester, First Time, Lisa is the worst girlfriend ever, M/M, Pegging, Sexual Fantasy, Some Humor, Straight Cas, Straight Dean, Straight dudes preparing for anal with each other, Supernatural Kink Bingo 2018, Top Cas
Language: English
Status: Completed
Published: 2018-06-21
Updated: 2018-06-21
Packaged: 2019-05-26 10:43:59
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 8,913
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14999189
Author URL: https://archiveofourown.org/users/zation/pseuds/zation
Summary: When asked for a dirty fantasy of his, Dean suggests pegging and promptly finds himself dumped by his girlfriend for it.Or,The one where Cas is more than willing to cheer up his best friend.





	What are friends for?

**Author's Note:**

> Okay, so pegging as I’ve understood it is basically a woman wearing a strap-on and fucking a man, right? So, how to write that when I prefer not to do M/F…?  
> I’m making Lisa out to be a huge bitch/asshole here but in reality I have nothing much against her lol  
> Sorry all Lisa fans!  
> Now, let’s have fun with straight!Dean getting fucked up the ass for the first time XD  
> (A special shout-out to my Beta, BeeCas, who gave me an incredibly helpful review on this one, I love you honey!)
> 
>  
> 
> **Square filled: Pegging**

 

 

 

Dean was mostly done dressing when Lisa finally got out of the bathroom. He grinned at her and whipped his Henley over his head before stepping up and kissing her quickly.

“You smell like roses.” He teased and she wrinkled her nose at him playfully.

“You should have joined me in the shower.”

Dean snorted and sat down on the bed to pull on his socks. “And risk slipping? No thank you, shower sex is out of the question since the spring of ’96.”

Lisa laughed and went to pick out some new clothes. She let the towel drop and Dean took a moment to admire her voluptuous body. She looked good and she knew it too, knew that Dean was looking and liked it, he could tell by the playful grin she threw him over her shoulder.

“So just because you slipped while sexing up some other girl it means I won’t get any?”

Dean stood to saunter up to her, circling her waist and kissing her warm skin lovingly. “Don’t I give you enough, sweetheart?” he said, pretend-hurt and she giggled when he brushed his lips up her neck in the way he knew would tickle her.

She turned in his embrace, batting away his grabby hands. “Oh you’re a handful alright.” She laughed again when he snatched her bra out of her hands before she managed to put it on. She didn’t chase him, though, and instead just pulled on underwear and a pair of yoga pants. Damn, her butt was just awesome…

“I dunno if I want you naked or in these pants more.” He growled and slid a hand down her body, groping her lightly and she smiled up at him.

“Cool it, tiger.” She kissed him, though. Deeply and damn, that felt good. “We just had sex, and I want to eat dinner.”

“And yet you were willing to go again if I had wanted to in the shower?” he laughed and let her go so she could get dressed too because dinner sounded nice.

“What can I say, I like it?” she grinned at him when he scrunched up his face. “How about this, if I indulge you in one of your fantasies, you’ll indulge me?”

Dean’s face lit up at that suggestion. Having one of his fantasies fulfilled? Hell yeah, that sounded awesome and hey, it wasn’t like he didn’t like shower sex in general. He just didn’t trust the slippery floor and last time had ended both him and his then-girlfriend in the ER with a possible concussion and a badly bruised (but thankfully not broken) knee. So yeah, he was adverse to it but only as a precaution. He could do it and especially so if he got something he wanted.

He tapped his chin thoughtfully as Lisa went about her bedroom getting herself ready to go out.

“Anything?” he asked eventually and she turned to him with surprise.

“You’re actually thinking about it?” this time it was her face that lit up. “Yeah sure. As long as it’s not like illegal or disgusting.”

Dean laughed and thought about scat and no, just no. “Actually…” he had one thing that he had always kind of wanted to try but he hadn’t felt comfortable enough with a partner before. There had been one girl (Rhonda Hurley) but she had moved before he had worked up the courage. He was sure she would have done it though, Rhonda was adventurous. And yeah, maybe Lisa wasn’t like that but Dean felt good around her in a way he hadn’t for a long time.

“Come on, Dean.” She said, her voice seductively lowered and hell yeah, Dean was so on board. “Just tell me and maybe we can do it already tonight.”

“Kinky.” Dean wriggled his eyebrows and his insides flushed hot at the thought that yeah, he was going to ask this. He might get his fantasy and with a hot woman like Lisa, no less. “Okay, I’ve always wanted to try pegging.”

There was a moment of pause and then Lisa blinked slowly at him. Dean felt like a dog, waiting happily for his master’s approval.

“Pegging?” she asked and if Dean hadn’t been so excited he might have picked up her hesitant tone already here.

“Yeah.” He grinned widely. “I’ve never done it but I’ve wanted to for a long time, do you know what it is?”

“Isn’t that…?” her brow furrowed and she looked down. “When a woman uses a strap-on dildo on… on a man?”

“Yeah, it’s—”

“So he gets taken up the ass, like…” she looked up and Dean’s excitement drained away slowly. “Like the gays do it?”

Gays? Not but it was a legitimate kink between heterosexual couples too, right?

“What? Lis, I—”

 

*****

 

“She didn’t have to dump me for it!” Dean was so angry and humiliated and _mortified_ he couldn’t even look his best friend in the eye while talking about this.

He was face down on Cas’ bed, having fled to his friend’s little studio apartment after Lisa shoved him out the door. Cas and Dean had been friends for a _long_ time and really, aside from maybe his little brother, Dean knew no one he could confide in as well as Cas. With Cas there was never any judgement.

But still, explaining that he was upset because his girlfriend of almost six months had broken up with him because pegging apparently was “too gay” was mortifying no matter how understanding Cas was.

“No, she did not.” Cas answered, his gravelly voice levelled and some people (who didn’t know Cas well enough) would think that he didn’t care. But Cas just had a very steady tone of voice and Dean had always thought it was kind of cool. When Cas spoke people listened.

Dean huffed and turned his head to the side on Cas’ pillow so he would be able to look at his friend where Cas was sitting at his desk.

“Or did she?” he asked in a low voice. “Maybe I am gay?”

Cas turned on his swivel chair and studied Dean solemnly. They were the same age but sometimes Dean thought it felt like Cas had lived several lifetimes already and he liked it, made him feel safe.

“I don’t think wanting to try pegging makes you gay, Dean.” He said eventually and yeah, Dean had thought so himself but hearing Cas say it made him feel better. Hell, he had never thought along those lines at all (lots of straight dudes got pegged, right?), not until Lisa had screamed it at him in a venomous tone. “And even if you have dormant homosexual tendencies it doesn’t make you a bad person, Dean. Besides, the sexuality spectrum is so wide that it’s hardly fair to put a label on you from this very isolated incident.”

To be quite honest Dean didn’t get all of that but he understood that no, he didn’t have to be gay because of this fantasy and also that Cas was trying to make him feel better. And possibly that Cas would be okay with Dean being gay? He was unsure about that one and he didn’t think he needed to think about it much either because he wasn’t gay so there, case closed.

“Thanks.” He muttered, eyes averted and Cas sighed a little.

“Honestly, Dean? If you had turned out to be a flaming gay man then I understand that a woman wouldn’t want to date you but Lisa shouldn’t have made that assumption and she most definitely shouldn’t have treated you the way she did.” He got up and sat down on the bed, placing a hand on Dean’s shoulder and it felt nice. Cas had very big and warm hands. “I’m sorry.”

“‘S nothin’ for you to be sorry about.” Dean mumbled. “I guess I’m just weird.”

“You’re not.” Cas said so confidently Dean wanted to believe him. “And I don’t think pegging is that unusual of a kink either. I mean, I’ve never tried it and I don’t know anyone who has but I still knew about it, right?”

“I guess.”

Cas sighed again and squeezed Dean’s shoulder. “I get it that you’re sad about Lisa treating you the way she did and I’m mad at her for it. I wish that there was something I could do to cheer you up.”

“Yeah…” Dean mumbled and thought about that gumbo he and Cas had eaten at _Benny’s Cajun Cookin’_ last week. That would be nice, he thought but didn’t have time to say so before Cas continued.

“How about I try pegging with you?”

Dean’s eyes snapped open and he rolled to his side so quickly he almost rolled off the bed. “What?”

Cas looked serious, although that was nothing unusual about that. “Or is it, ‘I try pegging you’? I’m not familiar with the terminology.”

“No, Cas.” Dean held up a hand and took a deep breath. “I mean, what are you talking about?”

“Pegging.” Cas deadpanned in his most deadpan-y voice and Dean almost choked on his own spit.

“I can’t have sex with you!” he squeaked and Cas looked… well not disappointed but rebuffed, at least for a second.

“I’m sorry, I was just trying to make you feel better.” He rose from the bed and Dean couldn’t help but feel how cold it got when Cas left his side. “I realize that it’s maybe too soon after your breakup and I wasn’t suggesting we do it right now. But I see that I was insensitive, I apologize.”

“No, but Cas.” Dean sat up and reached for his friend. Cas turned around when Dean brushed his hand against the other man’s arm. “We’re… we’re _best friends_. Wouldn’t that make it weird?” wait, what the fuck was Dean saying? The friendship wasn’t the thing here, okay? “Besides,” he pressed out, forcing a smile that probably only looked nervous. “Pegging is between a man and a woman, right? I… I’m _not_ gay, right? And besides, it’s supposed to be with a strap-on dildo.”

Cas frowned down at Dean like he did when he was deep in thought or displeased (or both). “I know that, but I figured I have something better than a dildo and we could emulate the act.”

Dean’s eyes of course drew down to Cas’ crotch and not only because Cas had referred to his dick right now but because when he was standing and Dean was sitting it kind of got in Dean’s line of sight.

“I… I guess you do.”

Cas shrugged and went to sit down at his desk again. “I’m not offended that you would say no, Dean. Just know that the option is there for you if you want to test it and can’t find anyone else. As a pick-me-up.”

And one hell of a pick-me-up, Dean thought as he watched Cas turn back to his studies. Who the hell would offer sex to their friends as consolation when their girlfriends dumped them? Then again, Cas was probably just feeling bad in general for Dean and didn’t want him to miss out on his fantasy and Cas had always been very straight-forward. If Dean was sad about Lisa there wasn’t much Cas could do about that but if Dean was sad about not getting pegged then yeah, he guessed Cas could kind of help with that.

He studied his friend for a moment but ultimately decided that nah, what a weird fucking thing to offer and even weirder to accept. They were bros, Jesus Christ.

 

*****

 

Three days later Dean barged into Cas’ studio apartment, wet from the rain outside and a plastic bag from the drugstore in hand, stuffed full of all the things he didn’t dare name out loud but had thought would be necessary for this to work.

“Dean.” Cas said, turning on his chair (was he always fucking studying? Yes, yes he was…). “What a nice surprise.” And it sounded like he really thought it was too. Well, Dean supposed he should have called ahead but he was too flustered, okay?

“Does the offer still stand?” he asked, his voice much gruffer than he had intended. He could barely meet Cas’ eyes and he was standing just inside the door, dripping on the cheesy doormat Dean had gotten Cas when he moved in.

“What offer…?” Cas frowned when Dean _wouldn’t look at him_. “Oh.” He rose from his chair but thankfully remained by his desk as if he knew Dean would get startled easily. Well, of course he knew, Cas knew everything about Dean (now, the pegging fantasy had been the last thing). “Are you drunk?”

“What?” Dean’s eyes finally found Cas’ and his friend looked at him with such composure that it calmed Dean down significantly. “No.” He drew a big breath. “No, I’m sober.”

Cas nodded once. “Then the offer still stands.”

Dean pressed his lips together for a moment and Cas let him collect himself. “I’m using your shower.” He practically barked and then stormed off to do just that.

Cas didn’t say anything and he didn’t follow Dean and Dean felt a bit bad about his behavior but he was so goddamn nervous he was almost nauseous but at the same time he was getting aroused too. It was a weird combination and he didn’t know how to handle it.

He barely knew how to handle the small bulb enema or the feeling of washing himself so intimately either but he managed. And _maybe_ the shower he took after using the enema was slightly longer than necessary but hey, he just wanted to be _thorough_. Hell, if he would have to worry about Cas getting poop on his dick he would never be able to relax.

That was why, he thought, it would probably be better with a dildo because dildos weren’t the real deal. Well, he had bought Cas lubed condoms so he would probably be good. And gloves for the prep but he didn’t think Cas would have to worry about that because Dean should probably do that himself.

He looked at the gloves and then craned his neck to try and look at his butt in the mirror.

“Maybe on the bed.” He muttered with a burning face and quickly packed the stuff and cleaned off the bathroom.

He entered the outer room in only his underwear and a t-shirt. Cas was sitting on his small couch, reading a book, and he looked up when Dean came closer. Suddenly very aware of the fact that Cas probably had heard him (the apartment wasn’t very big, after all), Dean blushed crimson and pulled at the hem of his t-shirt, looking to the side.

“I, um…” he drew a big breath. “I cleaned myself.”

Cas hummed and stood up, coming closer than Dean had anticipated. “That was very thoughtful of you.”

“It’s just good etiquette.” Dean sniffed and saw how Cas smiled to himself. “In any case, I, um, I haven’t prepped or anything so I’m just gonna do that.”

Cas stopped him with a hand on his arm when he went to put down the bag by the bed.

“Don’t hide, Dean.” He said and damn, was his voice always so… well so fucking inviting and smooth?

Dean blinked at him. “I ain’t, I’m just saying I’m gonna loosen my ass or whatever and we can—”

“Dean.” Cas pulled him in by his arm and Dean stumbled back against the other man’s chest. “I’m trying to tell you not to worry, I can do it.”

Dean stared at Cas for a moment, at his _best friend_ who apparently knew all about this, what the fuck?

“Uh, what?”

Cas smiled indulgently and gently took Dean’s bag from him, going over to the bed. “After you left last time I started thinking that you might change your mind. And maybe we would do this, you know?” he looked at Dean with a strange gaze. It was somewhere between lust and kindness and for some reason it kind of set Dean on fire. “And I realized that while I know _of_ anal sex, I don’t actually _know_ it so I read up on the subject.”

“You…” there was so much Dean wanted to address right now but one thing at a time. “We’re not having anal sex.” Okay, that was probably not the most prominent thing here but the definition felt important to Dean. Lisa’s scalding words were still too fresh in his mind.

Cas rolled his eyes in a way he most definitely had learned from Dean. “Right, what I actually I meant was that while I know _of_ pegging, I don’t actually _know_ it so I read up on the subject.”

“Don’t be smart with me.”

Cas busied himself with emptying the bag’s content on his nightstand and adding to it with stuff he got from a drawer.

“My point is that I know we will have to stretch your hole and that the experience can be painful.” He looked up, all serious and the look was good on him (had always been good). “And even when we have stretched you it can be painful. I want you to enjoy this if we do it so I read about it and I tried it.”

“You…” Dean’s mind suddenly ran wild with images of Cas hiring a hooker to be all pragmatic with. “What?” ugh, he hated when his voice got all squeaky like that…

“On myself.” Cas deadpanned as if he had seen Dean’s every dirty imaginary version of him with both men and women. “I bought some KY and stretched out my own hole. Oh, and I found the prostate so we’re doing that, it was amazing Dean.”

Dean stood there, gaping like a goddamn goldfish for a long moment. Long enough that Cas managed to get mostly undressed, he was down to his boxer-briefs when Dean finally snapped to attention but holy fucking hell, the mental image of Cas doing that to himself was just…

Well, to be frank Dean wanted to shriek 'TMI!' at the top of his lungs and maybe rinse his eyes with vinegar but even more than that he could feel himself growing aroused for exactly two reasons. The first (and most fucked up) was that the thought of Cas enjoying having fingers up his ass and finding his prostate was weirdly hot. Cas _never_ got ruffled and… and it had kind of sounded like he had been when he did that to himself.

And the second reason was simply because holy shit, Cas had kind of planned this. Not for this to happen exactly but he had prepared for the eventuality that it _could_ happen. Because he didn’t want Dean to have a bad experience, because he wanted Dean to be comfortable and feel safe and… and Dean didn’t know why that was a turn-on but it fucking was, okay?

“Really?” he squeaked and didn’t even care about the tone of his voice now. “You’ve… you just went and did that, huh?”

Cas nodded and indicated the bed with a sweep of his hand. “I feel confident that I can make you feel good, Dean.”

“Y-yeah. Yeah, that’s good…”

“When I peg you.”

“Jesus Christ, Cas!” Dean exclaimed and buried his face in his hands. “Maybe this isn’t such a good idea.”

“Why not?” when Dean looked up Cas was frowning at him and that felt wrong, Cas was only trying to be helpful in his own way.

“I just… it’s just embarrassing, okay? Lisa fucking dumped me for wanting to try something like this and now we’re gonna do the exact thing she accused me of wanting? Maybe it’s too much?”

Cas drew a deep breath before coming to stand before Dean, one hand on each of Dean’s upper arms.

“Only you can say if it’s too much, Dean. Don’t worry about me, I’m completely willing and I think both of us will find this enjoyable if we just let us but if you don’t want to then we shouldn’t.” He smiled and it was his special smile, that little one that always made Dean feel appreciated. “I know what we’re about to do isn’t the same as a woman putting on a strap-on.”

Dean blew air out of his nose harshly, fed up with his own insecurities. So what if Lisa had accused him of being gay? For one, this pegging fantasy of his wasn’t about sexuality and secondly, even if it was there was nothing wrong with it.

“I already rinsed out my ass, let’s do this.”

Cas laughed, low and surprisingly pleasant (because it wasn’t like Dean hadn’t heard him laughing before but okay…) and stepped away to pick up the KY he apparently had already opened.

“Great, then get undressed and lie down on your stomach.”

“I bought gloves.” Dean mumbled as he did just that. The sheets smelled very clean and Dean wondered for a moment if Cas had changed them while he was in the bathroom. His stomach squirmed pleasantly at the thought and he decided not to ask. “For the prepping.”

Cas frowned down at the rubber gloves as if he didn’t even know how to use them and then he put them to the side.

“You said you cleaned yourself, right?” he asked and Dean buried his face in Cas’ pillow, nodding. “Well, I rinsed my hands in the kitchen sink and I’ve checked my nails so we’re good to go.”

“Can you please stop making this sound so clinical?” Dean said exasperatedly, his words muffled against the pillow.

“I’m sorry.” Cas chuckled and Dean heard him puttering about and then suddenly Cas’ warm hand was on Dean’s hip. “Raise your ass for me, Dean.”

Dean’s whole body froze at the change in Cas’ tone. He whipped up his head, staring at his best friend because holy fucking hell, who knew Cas could sound so sultry? So… so whisky-rough and inviting. He gave Dean a smile and goddamnit, that was a smile Dean had never seen on Cas’ face before. It made him seem like this otherworldly creature come to give Dean the pleasure of his lifetime and how the fuck could a single smile do that?

He gave a full-body shudder and did as Cas asked him to. He felt red in the face because of the fact that he was already chubbin’ up a bit but Cas apparently wasn’t after that. Instead he just slid a pillow from the couch under Dean’s hips so that when Dean relaxed again his butt was elevated.

“This feels weird.” He muttered and rolled his hips in place for a moment, trying to settle his dick so it wouldn’t get smushed.

“It’s for easier access.” Cas said and put a hand (a warm, _warm_ hand) on Dean’s lower back, immediately stilling him. “You look very good like this.”

Fuck, his voice was still low like that and Dean couldn’t help but shudder with pleasure again.

“Y-you don’t have to seduce me or nuthin’…”

Cas chuckled but this time it sounded much more… _seductive_ for a lack of a better word (and believe Dean when he said he wanted a better word). Dean hugged Cas’ pillow and hid his face again when he felt Cas settle on the bed behind him.

“Better like this than clinical like before, yes?”

Dean didn’t know about that, actually. Clinical took the fun out of it but like this Dean’s mind got weird and it started to feel like something other than a friend just helping out a friend. Started to feel like something more (because Cas had _planned_ for this) and Dean didn’t know what to make of that.

“‘M not gay.” He closed his eyes when he realized he had said that out loud.

“I didn’t say you were.” Cas continued in his whisky-voice, his palms warm as he touched Dean’s butt. “I just want you comfortable.”

“I know, Cas.” Dean breathed because oh, it felt nice the way Cas was touching him right now.

He swept his palms across Dean’s ass and lower back in arches, massaging the meat and making Dean go all gooey. He melted down against the bed, elevating his ass even more when Cas encouraged him to arch his back.

He bit his lower lip when Cas dipped his thumbs into Dean’s crack and he couldn’t help but clench his hole. It would be an intrusion he was highly unfamiliar with but at the same time he wanted to feel Cas there. Cas had very long fingers, slender and capable.

The next time Cas dipped lower Dean shivered and subconsciously spread his legs a bit.

“You okay?”

“Yeah.”

Damn Cas for knowing how to use his hands and voice to make Dean all foggy like this. Maybe he should have prepped himself… Dean was starting to actually crave Cas’ touch back there and shouldn’t that feel like too much? On the other hand, if he had done this with Lisa, wouldn’t it have been awesome if she had done the prepping? It left Dean exposed and he thought, as Cas spread his cheeks slightly, that being exposed was probably half of the fun for him.

Cas grabbed one ass cheek in one of his big hands and trailed down Dean’s crack with the fingers of the other. He didn’t press or prod, just danced his fingers down the crack, over the hole and down Dean’s taint to his balls where they lay snug against the pillow. It made Dean shiver again and he licked his lips when he realized he had been breathing through his mouth (not quite panting but close enough). His whole body felt chilled and on edge from Cas’ light touches and he liked it, made him aware.

“You have a very nice color.”

“You don’t need to praise me.” Dean bit out and realized the moment he had said it that he kind of liked it when Cas did that. Lucky Cas had a streak of ignoring Dean’s bullshit.

“Look at your balls.” He mumbled and brushed his thumb across them. “So full.”

Dean had to choke off a fucking moan. Okay, so he hadn’t spanked the monkey in a while (Lisa had put a pretty big dent in his confidence…) and he was fucking aroused, okay? Didn’t mean he had to sound like a fucking whore.

“Sorry they’re there, I can’t like tuck them away or whatever.”

“What do you mean?” Cas sounded seriously curious. Dean drew a deep breath when Cas pulled away only to pick up the KY, by the sound of it. “Are you uncomfortable?”

“No, I just mean…” Dean huffed and was glad they were doing this in this position so he wouldn’t have to show his stupid face. “They’re probably not so nice for you to look at.”

“I think they look wonderful, Dean.” Cas stated and then surprised the crap out of Dean by touching him with suddenly lube slick fingers. Dean made an embarrassing _hiiiih_ sound but Cas just ignored it (thank God). “They have a very nice color and they fit between your legs very well. In fact,” he raised himself on his knees, Dean could tell by how the bed dipped, and pressed his lubed hand harder against Dean’s crack. “I think you look very good like this, Dean.”

“I-I dunno, Cas…”

“I’m going to insert one finger now, Dean.”

Dean wanted to bark at him not to narrate but the truth was that it calmed him down. Prepared him for the feeling of Cas’ finger pressing against his hole. Cas just rubbed there for a moment and Dean forced himself to release a breath he hadn’t been aware of holding. As soon as he relaxed his ass, Cas dipped inside. Almost as if he had known Dean was tensing up and was doing his best not to.

The thought that Cas was waiting for him made Dean feel much safer than he had thought it would and it helped him relax further. Cas’ finger slid mostly easily in up to the first knuckle and holy fucking shit, Dean had someone’s finger in his ass (someone not a doctor and fucking hell, it was _Cas’ finger_ ).

“C-Cas…” he stuttered and gripped Cas’ pillow so hard his knuckles went white.

“It’s very tight.” Cas stated in a rough rumble and Dean felt his dick lurch at the thought of how Cas might be affected by this. In fact, Dean just realized that for this “pegging” to work Cas would have to be hard enough and was he even sure he could manage that? Dean wasn’t sure he would be able to get it up for another dude but then again, he was hard against a pillow just at the feeling of Cas’ finger in his ass and Cas’ rough voice so…

“‘M okay.” He pressed out, his eyes squeezed out. “It doesn’t hurt.”

“Tell me if it does.”

Dean’s hum of agreement turned into a broken little moan when Cas pressed in even further, his clever finger reaching places Dean had barely dared touch even in the earlier shower. His whole face flushed red hot at the thought of Cas being inside him like this, of _feeling_ Dean inside and out.

His whole body trembled and for a moment he tensed up, making Cas still his hand, and when he relaxed again Cas pulled out slowly. Arousal burned through Dean but at the same time the feeling was so foreign and yet so familiar he couldn’t help but feel anxious. What if he wasn’t clean back there? What if…?

“Relax for me, Dean.”

He did so while breathing out harshly. “Cas, I…”

“You’re doing very well, Dean.” Cas said and damn, was his voice even huskier? Dean buried his face in the pillow and arched his back again. “I will go in again.”

With more lube apparently but hell, it wasn’t like Dean thought they could have _too_ _much_ lube. Cas worked his finger in and out slowly, feeling around inside, sometimes pausing to press his whole hand against Dean’s body.

Dean melted down on the bed again, slowly getting used to the feeling and actually enjoying it. They were both mostly quiet, Cas’ breathing loud in Dean’s ears and Dean sometimes giving an involuntary sound of pleasure but nothing was said and Dean didn’t know if that was good or not. All he knew was that he was getting more and more aroused and the pillow they used to elevate his ass was pressing against his dick in a way that had been uncomfortable for a while but was starting to feel good.

“It’s almost as if you’re sucking me in.” Cas said just as he pulled all the way out again and the way he sounded, all fucking breathless and whatnot, made Dean moan loudly despite himself. “I’ll use two fingers now, Dean. I’m not that big but I think I want to use three fingers on you before we try to move on.”

Dean could do nothing but nod, too embarrassed by Cas’ narration and for some fucked up reason turned on by the same.

At the same time as he put two fingers against Dean’s hole, Cas gently grabbed Dean’s full balls, brushing them with his thumb as he pressed inside. The dual sensation had Dean on edge and he moaned again, more uncaring of the fact as pleasure spread out from his groin and seeped into his every limb.

With two fingers Cas could apparently reach more and he moved faster now, spreading his fingers occasionally to loosen the muscle and fucking hell, Dean hadn’t thought it would work but it damn well felt like it did. And it didn’t even hurt, no Cas was so gentle in his ministrations that Dean would have relaxed completely if it weren’t for the fact that he was getting more and more aroused. Because if this part went well (which it sure as fuck seemed to) then that meant they would soon move on to the next and shit, Dean was about to get pegged and he wanted it so much.

And then Cas brushed _something_ inside Dean and he almost shot right off the bed. Cas quickly grabbed Dean’s hip and pulled him back down and yeah, Dean was struggling but not against Cas’ grip, just in… in fucking general because what the hell?

“Cas!” he gasped sharply when Cas pushed that _thing_ again. His dick jumped and he felt himself blurt out so much precome he was sure he stained the pillow under him. “The _fuck_?”

“Prostate, Dean.” Cas answered calmly, though his voice was still as rough. “I told you, didn’t I?”

Yeah, he had said it was amazing but he hadn’t told Dean _how_ amazing. Fucking hell, it felt like his dick was being petted from the inside and damn, he couldn’t breathe. He was humping back against Cas’ fingers before he knew it and yeah, now he could see why people would do this to themselves. Part of the fun with pegging (for Dean) was definitely giving up control, feeling vulnerable and exposed, but this… this was sure to fucking amp it up.

Cas didn’t touch it all the time, he alternated between poking it, rubbing it, bypassing it and making Dean chase him, and damn it felt good. Soon Dean was harder than ever and leaking and spreading his legs like a hooker and not caring one bit. He just wanted Cas’ fingers against his prostate and couldn’t stop moaning about it.

“Do you think you can take another finger?”

Dean didn’t know if he was projecting or not but Cas sounded breathless and fucking stunning right now.

“Yeah.”

Three fingers felt like a stretch, though, even with how much Cas had already prepared him and with how much Dean wanted him inside and prodding his prostate. He groaned, both in discomfort and arousal and Cas of course seemed to pick up on it. He stilled his hand and used his other to brush up and down Dean’s back and sides.

“You’re taking my fingers very well.” He murmured and Dean blushed crimson. Fuck he wanted more but he didn’t know how to ask for it.

“Do we have to do this much longer?”

“Don’t you like it?”

Dean gritted his teeth because Cas should know how much Dean liked it by now. He just nodded and bumped his ass back to get Cas to start moving. He did so slowly but soon quickened his pace when Dean couldn’t help but grind back and moan.

“I want…” fuck he couldn’t say it. “More.” Or maybe he could?

Cas breathed out so harshly Dean felt it flow over his back and he liked the sensation. When he sneaked a peek over his shoulder (the first since he laid down) Cas had his eyes closed and his mouth slightly open. He looked a cross between concentrated and enraptured and fuck, desire shot through Dean’s body so fast he whipped his head around to bury his face in the pillow.

“Can you take it? I don’t want you to hurt.”

Dean thought he should probably ask if Cas was even hard but he thought his friend had the wits enough to say if he wasn’t.

“I can take it.” Fuck his voice was raspy all of a sudden but it was the realization, he thought as Cas pulled out. Because with this admission he had given Cas the green light to fuck him in the ass, right? No, pegging, Cas was going to…

Dean groaned, his face still hidden and his groan muffled. No, Cas was going to _fuck him_ and Dean wanted it. Well, to be honest he wanted more stimulation on his prostate but somehow fingers seemed insufficient. He wanted to be used and held down.

Cas stepped off the bed, presumably to remove his underwear (by the sound of it) and then he was standing by the nightstand, effectively putting his groin at level with Dean’s head. And Dean couldn’t help but sneak a look, okay?

What he saw almost made him choke. If he had been nervous about Cas not being hard enough he was proven dead wrong because Cas’ dick looked hard as iron, ramrod straight, red and leaking at the top. His balls were tight and round and fucking hell, _why hadn’t he said something_? Clearly he was feeling it and Dean would have wanted to know, okay? He should tell Cas to tell him next time. Wait, what…?

“Do you want to use the condoms you bought?”

Dean snapped his eyes up to meet Cas’ but the man was looking down at the unopened package in his hands.

“Yeah, I—” he had to clear his throat once. “They’re lubed.”

“Yeah that’s probably smart.” Cas mumbled and broke the seal. “I was just wondering because I have regular condoms if you didn’t want to open a new package.”

“Nah, I bought them for this, so…”

Fucking hell, Dean couldn’t even look Cas in the eyes, he was both embarrassed and aroused. And wasn’t that the fucking theme of the evening? But shit, he was talking to his best friend about which condoms would be best for when his friend would fuck him up the ass and—

Dean took a deep breath and nuzzled against the pillow just as Cas sat down again. He needed to calm down. The only fact he had to focus on was whether or not he found this enjoyable and judging by the sizzling arousal that set his whole body on fire he totally enjoyed this. He just needed to get out of his head for a while.

Actually, them talking so normally about the condoms as if Dean hadn’t just been moaning like a two-dollar whore while fucking himself on Cas’ fingers had felt kind of nice. Felt grounding.

“Do you need me to get on my knees?”

Cas hummed and Dean heard the condom wrapper being torn open. “Maybe a little? Get some leverage under you and, yeah like that.”

Dean felt ridiculous but then Cas’ hands were on his ass again and Dean’s focus shifted real fucking quick from his weird position to the warmth of Cas’ hands. He slid them from the meat of Dean’s ass to his hips as he shifted closer and Dean’s heart was beating like a humming bird’s. He froze when Cas’ dick brushed up against his thigh but Cas didn’t say anything about it. He just used his strong hands to pull Dean into a better position and the feeling of the (slight) manhandling made Dean flush with pleasure.

“Go easy.” He mumbled and Cas took a moment to press three fingers in again.

“I’ll just dip the head in.”

“You’re not testing the water.” Dean muttered and it made Cas chuckle, surprisingly.

“I think we’re both nervous.” He said in a soft tone that made Dean relax some. “I’ll start with the head because it’s basically thickest.”

“And at the tip.” Dean didn’t know why that made Cas chuckle again, it was true right? It wasn’t like he could start with the base of his dick.

And then Cas was nudging the blunt head of his dick against Dean’s tiny fucking hole and Dean wasn’t thinking about semantics anymore. Because holy fucking hell, Cas felt _huge_ all of a sudden and how was that true? Dean had seen Cas naked on a number of times before (although never hard before tonight) and he was right in saying he wasn’t super big. Average was probably the most apt description, but shit right now he felt humongous.

And that thing was going _inside Dean_. He gritted his teeth, feeling the vein on his throat budge out as he tried his best to relax and bear with it but damn if it wasn’t hard. Cas paused after just the head was inside and Dean thought that yeah, okay, this could work, but then Cas pressed more. Inch after inch and fucking hell, how the fuck long was he even? The more Cas pressed in, the more Dean’s own erection waned because fucking hell, he had never felt stuffed full like this and he didn’t even know what to think of the feeling. Confused, mostly.

Cas grunted lowly when his pelvis hit Dean’s butt and fuck, that meant he was in to the hilt. Completely filling Dean up and was this how women felt like? Only, like, in the vagina instead? Dean didn’t know what to think about that comparison either and he breathed as evenly as he could to calm down, his heart feeling as if it was going to beat out of his chest.

“How does it feel?” Cas asked after a moment, his voice strangely strangled in a way Dean kind of liked.

“Like I’ve got shit up my ass.”

Cas laughed and the act made his dick jump inside Dean. “Not very good then?”

“I kinda feel constipated.”

Cas hummed and stretched out more over Dean, hands gripping his hips hard and when he moved he inadvertently pressed Dean’s dick down against the pillow and okay, that still felt nice.

“Do you want me to pull out?”

Dean bypassed Cas’ curiously thick tone to assess the situation. In a way he kind of wanted Cas to pull out completely but at the same time he still wanted to try this. In this position Cas wasn’t pressing against Dean’s prostate (which Dean thought was bullshit, Cas was clearly thick enough to manage that because Dean’s ass wasn’t _that_ wide) and he thought that if they managed that he would feel better. Still, he might have hoped the feeling of being full would have been nicer in itself.

“It’s not… it’s not _that_ bad.” He didn’t really know what to say. The more they stayed like this, the more he got used to having Cas in there though and he thought that was good.

He only noticed that Cas was shivering when Cas swept a trembling hand up and down Dean’s side.

“I’m only asking because I’m approaching the point of no return.”

“What?”

In fact, Cas’ whole body was shuddering and he was burning hot, his dick hard in Dean’s ass.

“I want you to feel good Dean, but if we continue much further I fear I will lose my mind. I don’t want to hurt you so if you don’t like this we should quit now.”

Dean couldn’t breathe for a moment there. Was Cas actually saying what Dean thought he was saying…?

“You’re enjoying this _that_ much?” his voice came out in a hoarse whisper and he looked over his shoulder when Cas huffed out a chuckle.

“Isn’t it obvious from my erection?”

“Well…” well yeah, Dean supposed and shit, looking at Cas now Dean thought he had never looked more handsome. His face was flushed and his hair was spiky. He almost looked like a man possessed, like he really would lose his shit any second and Dean suddenly wanted that. Wanted Cas all ruffled and hot and bothered and all because of Dean. “We’ve already come this far.” He mumbled, voice suddenly intimate and Cas’ infinitely blue eyes snapped up to meet his, making a pleasant shiver run through Dean’s body. “Come on, Cas. _Peg_ me.”

Cas breathed out harshly and then proceeded to do just that. He pulled out slowly at first but then slammed in hard, groaning deeply. Dean yelped at the pace Cas set but he didn’t regret it, neither the pace nor the way Cas gripped Dean’s hips to pull him into each thrust. Who the fuck knew Cas would be the kind of guy to fuck like this? All wild and with no abandon and goddamnit, it was clear that he possessed the core muscles to back his pace up and that he was willing to put them to the test.

Each thrust was long but not slow in the least, his hips pistoning so sharply his hip bones smacked loudly against Dean’s butt, filling the room with the sound of their loud breathing and their bodies coming together wetly. And holy fuck, Dean thought he could feel every part of Cas’ dick from the vein on the underside to the ridges in his head. He felt huge and somehow the prefect size at the same time and Dean couldn’t grasp how that was possible.

At this point he felt like he could do nothing but moan and spread his legs, suddenly more than willing to just lie there and let Cas use him. Cas’ breathing was ragged but clearly not from exertion and Dean fucking loved feeling the man’s breath on his back again. One small tilt of Dean’s hips and Cas was back to poking Dean’s prostate too, only this time with his hard dick and fucking hell, that felt so much better.

“Fuck yeah.” He moaned, face smashed against Cas’ pillow. “Right fucking there.”

Cas practically _snarled_ over him, grabbing Dean’s hips harshly, pinning him to the bed as he thrusted harshly into him. Dean wailed and felt his own dick quiver, erection more than revived in the face of Cas’ carnal lust. The pure onslaught of pleasure that seared through Dean’s body was almost enough to make him go blind and he didn’t fucking _understand_ how the fuck could this feel so fucking good.

Just a moment ago he had felt like he was about to goddamn poop the bed for fuck’s sake and now he was crying out, begging Cas in a hoarse voice to go faster, harder, deeper. And Cas was this fucking beast behind him and maybe that was the thing. Because Cas never lost his cool. Cas was calm and collected and meticulous.

And now he was a _beast_.

“Because of me.” Dean gritted out, each word punched out of him and Cas surprised him by draping his warm body over Dean’s back.

“Yes Dean.” He rasped against Dean’s ear. “You’ve made me so hard; it feels so good the way you take me.”

Dean fucking _keened_ and arched his back, the movement hindered by Cas’ weight but it didn’t go unnoticed by the other man. Cas groaned deeply and slowed his merciless pace to a deep grind, still in and out in some measure but mostly his hips just undulated and Dean saw stars with how the motion made Cas’ dick rub against his prostate continuously.

His dick ached against the pillow under him and he could feel his balls drawing up more and more with each grind against his prostate. He felt his arousal like a coil in his lower abdomen, slowly curling tighter and tighter, chills and hot streaks flushing over him in waves that stole his breath away as his orgasm kept building beyond his control.

“Fuck Cas, it feels so fucking good.” Dean’s speech was slurred and he didn’t even fucking care, Cas obviously understood enough anyway.

“Yeah?” there was both relief and arousal in Cas’ voice and it lit Dean’s body on fire. “God Dean, you feel so perfect around me. You’re going to make me come so soon.”

“Y-yeah?” the thought of Cas coming _because_ of Dean sure as fuck concentrated that fire in Dean’s groin that he knew that would only end one way. “How ‘bout a reach-around, huh?”

Well shit, he hadn’t meant to say that out loud but now that he had he wanted it more than anything and Cas didn’t seem to mind. He raised himself on his knees, pulling Dean up with him and a moment later his large hand wrapped around Dean’s leaking dick.

“So wet for me.” Cas groaned and Dean wanted to quip that that was something you told women but what was the fucking point? He _was_ wet, the pillow was wet, and he was going to come in Cas’ hand any fucking second with how expertly Cas flicked his wrist.

He fucked into Cas’ hand even as Cas pushed mercilessly into his ass and the slide was so smooth now, so perfectly slick that it blew Dean’s fucking mind. It had been so _tight_ and it still was, fucking hell it was so tight with Cas up there but it didn’t hurt anymore. It felt so fucking good Dean’s fucking mouth watered for some goddamn reason.

Suddenly Cas squeezed Dean’s dick even tighter, his other hand slipping on Dean’s hip as he slammed forward harder than a moment ago. “Dean, I—” he cut himself off with a new groan, much deeper this time, and Dean felt Cas’ hips stutter erratically for a moment.

 _'He’s coming',_ Dean thought desperately, his own dick expanding in the wake of his own orgasm. _'He’s coming in my ass, because of_ me _.'_

Dean’s breath left him in a big whoosh and in the next second he came his fucking brains out, completely overwhelmed by the fact that it was _him_ , it was _his body_ that had made Cas blow. Cas made a surprised sound and obviously did his best to jerk Dean off even as he was still coming himself and in a way the whole thing was one big clusterfuck and in another way it was the best fucking thing that had ever happened to Dean.

They both collapsed to the side and Cas slipped out of Dean with a slick sound and the weird feeling of having something come out of your ass but other than that Dean was completely fine with the way they ended up in a half-spooning position. At least they had managed to avoid the wet spot.

Dean looked at it as they lay there panting, feeling strangely proud of marking up Cas’ bed like that.

“I came on your comforter.” He stated at length and it was such a weird fucking thing to open with that he couldn’t help but chuckle along with Cas’ carefree laugh.

“That was probably the best lay I’ve had in a while, Dean.” Cas stated then, sounding about as serious as he was able to right after laughing like that and though Dean could do nothing but agree he couldn’t very well say it out loud. So he just nodded and rubbed his back against Cas’ chest until the other man slung an arm around his waist to pull him in closer. “Though I suppose as peggings go it was probably terrible.”

Dean huffed out a smile and turned half-way to look at Cas over his shoulder. “I suppose if I had been pegged by a woman she wouldn’t have come before me.”

Cas looked seriously at him. “That was an oversight on my part; I didn’t expect you to be so sexy.”

Dean blushed real fucking hard, that was true, but he kind of liked it so he just grinned at his friend.

“You’ve known me for like two thirds of your life and you’re just now figuring out I’m practically Adonis, shame on you.”

“You’re right.” Cas’ solemn face had always looked kind of cute to Dean. “I’ll work on that.”

“Yeah?” Dean turned more, coming face to face with a surprised Cas. “Next time I’ll come first?”

Cas looked stunned for a moment and Dean waited anxiously because what the hell, Winchester? Why did he have to go and ask for the whole arm when Cas had just offered his hand?

And then Cas smiled and fucking hell, Dean had never felt so relieved. “Yes, next time I will be better prepared.”

“Good.” Dean pretend-sniffed. “I guess we’ll call this the beta version. Next is beta 2.0.” He looked somberly at his friend when Cas got a mischievous look in his eyes. “Is this… is this going to make things weird?” he felt like such a little _girl_ for asking but Cas was his best goddamn friend, okay? That stuff was important and not to be fucked with more than necessary.

Cas drew his eyebrows together in thought. “I don’t think it has to, do you?”

Dean thought maybe he _should_ think it was weird already as it was and the thought that he wanted another go should probably make it even weirder. But he also blamed Lisa’s reaction to pegging for that feeling and when he thought about it seriously there was really only one answer.

“Nah, I’m good.”

Cas grinned, that grin where his whole face scrunched up and his gums showed and fucking hell, who knew he would be so happy from hearing Dean agree with him on this? Now Dean kind of wanted to give Cas the goddamn moon or whatever.

“And we don’t have to make it something it’s not.” Cas added after a sappy moment where they’d just been staring at each other (who the fuck even did that?). “We can just be two straight guys fucking around with each other and beta testing pegging the only way we know how.”

Okay, time to ‘fess up, Dean had always had kind of a thing for Cas swearing.

“I like the sound of that.” He laughed and Cas grinned again, wide and beautiful.

“I’m going to kiss you now.”

Dean fucking _squeaked_. “Don’t you think we should save that for the 2.5 version?”

Cas apparently didn’t and if he was being completely honest, neither did Dean.

 

 

 

 


End file.
